Key West Vacation Rentals

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Search nearly 100 Key West vacation rentals ranging from intimate 2 bedroom cottages to large 6 bedroom homes. With properties in popular Key West communities like Truman Annex, Key West Golf Club, and 1800 Atlantic plus a variety of pet friendly and monthly rentals, we are sure we have the perfect fit for your trip. Our local Key West team of vacation rental experts has been helping travelers plan amazing vacations for decades and loves to share their local knowledge. Don't hesitate to contact us with questions or for help finding the perfect rental and booking your Key West vacation!

Displaying 37 - 48 of 88 rentals matching your search criteria
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Verandah

Type

  • Home
2 Bedrooms
2.5 Baths
4 Guests
Beautifully designed yet comfortable private home that you may never leave, only to go outside to your private pool and secluded space to hang out.

Conch Wind

Type

  • Townhouse
2 Bedrooms
2 Baths
4 Guests
CONCH WIND - Stop searching, Conch Wind is the rental home in Key West you have been hunting for!

Ecco Domani

Type

  • Home
3 Bedrooms
2.5 Baths
6 Guests
Beautifully designed and decorated this private home has the gourmet kitchen with French doors that lead to your private outdoor space and pool.

La Casita

2 Bedrooms
1 Bath
4 Guests
The location of La Casita cannot be beat -- right in the heart of Old Town yet on a quiet lane, only steps to Duval Street.

President's Walk

Type

  • Townhouse
2 Bedrooms
1.5 Baths
4 Guests
It wasn't that long ago that President Truman took casual walks in this same location- now it's your turn! President's Walk exudes luxury and elegance with lots of upgrades and plush furnishings with your every comfort in mind.

Emma's Escape

Type

  • Condo
2 Bedrooms
1 Bath
4 Guests
Lounge your days away by the pool or enjoy the peace and quiet away from the hustle and bustle of Duval Street.

Nautical Dreams

Type

  • Cottage
2 Bedrooms
2 Baths
4 Guests
Nautical Dreams is the perfect spot for whatever you desire - parties or peace and quiet in a Key West vacation home.

Treetop Paradise

2 Bedrooms
2 Baths
4 Guests
Located in the historic Bahama Village neighborhood, nestled amongst the palms, you‘ll find the stately building that houses Treetop Paradise.

Poolside Paradise

Type

  • Home
2 Bedrooms
2 Baths
4 Guests
Spending time in the warm breezes of Key West – isn’t that why you come here? At Poolside Paradise you can enjoy outdoor living at its best!

Conch Condo

Type

  • Condo
2 Bedrooms
2 Baths
5 Guests
Perfect rental for a small family or couple of friends, close proximity to the pool and beach, Conch Condo makes one of the most desirable vacation rentals

A two-bedroom, two-bath condo in Truman Annex.

Duval Breeze

Type

  • Townhouse
2 Bedrooms
2.5 Baths
6 Guests
Location! Location! Location! Duval Breeze offers the best location in town! Walking distance to restaurants, bars and galleries and easy biking distance to the beaches!

Crowner's Jewel

Type

  • Townhouse
2 Bedrooms
2.5 Baths
6 Guests
Imagine being able to walk to the Sunset Celebrations every single evening! Only couple blocks to Mallory Square you can find this true gem!

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